Get Back Into The Parrothead Mindset In The Place That Does It Best

At its core, Jimmy Buffett's Margaritaville is a feeling, not a place. In fact, the official Margaritaville website states that "it's in the tropics somewhere between the Port of Indecision and Southwest of Disorder." This imaginary, no-passport-required, feel-good place is where "palm trees provide the camouflage... and island music rules."

But a stay at Margaritaville Beach House Key West combines the best of both worlds—a blend of laid-back attitude infused into a cozy resort with a margarita-in-hand vibe. 

Stretching along the waterfront across from Key West's largest beach, the 186-room Margaritaville Beach House truly runs on island time. This secluded escape with easygoing charm delivers warm hospitality and fun amenities, whether you're chillin' in the lagoon-style pool, swaying in a palm-shaded hammock, or sipping a frozen concoction by the firepit. 

The casual luxe property sets the tranquil tone as soon as you pull up to the main entrance, where you're greeted by a giant Blown Out Flip Flop sculpture with a pop-top tab laying at its feet—a nod to Buffett's iconic song lyrics. Nearby, you'll find a rack of bicycles to borrow—perfect for exploring the area on two wheels. 

Step inside the airy lobby and look up to see the attention-grabbing chandelier made from—you guessed it—margarita glasses. With a soothing blue and white color palette, the lobby beckons you to unwind the moment you step inside. (If you're a true Parrot Head, stroll over to the photo wall for a montage of Buffett images through the years.) As you check in, you're greeted with a welcome cocktail—a refreshing margarita (of course!) or a delicious mango mocktail. 

Congratulations! You're officially on island time.

Meander along the property's winding paths and you'll find shade-covered hammocks and Adirondack chairs dotting the landscape, inviting you to kick off your sandals and rest for a bit. This family-friendly (and pet-friendly) resort offers plenty of ways to both have fun and unwind—depending on your state of mind. Work out in the 24-hour fitness center, get some retail therapy in the on-site provision shop, tune in to the daily entertainment, and gather your companions for lawn games (think cornhole in the shade-dappled courtyard). 

Need a respite from the sun? Grab a table under the tucked-away tiki hut—a classic palapa that's typically reserved for an intimate wedding, private reception, or corporate meet-and-greet. But when there are no events on the books, guests can grab a table, pull up a chair, and chill with a cold drink or a summer beach read under the spacious thatched roof gathering space aglow with soft string lights above.

At the lagoon-style pool—appropriately named Fin's Up—you'll spot a crow's nest peering above the waterfall, another nod to the "island escapism" lifestyle Margaritaville promotes. Surrounded by lounge chairs, umbrellas, cabanas, and palm trees, the pool serves as the resort's centerpiece, with pool-view rooms overlooking the splashy tropical courtyard. On a scorching Keys day, you'll appreciate the daily freebies to chill you out—fruit smoothie samples at noon and popsicles at 2:00 pm. Yes, please!

When you're hungry, just walk up the steps to The Tin Cup Chalice Bar & Chill, the full-service, covered-patio restaurant with a relaxed vibe. The Old Key West-inspired veranda provides a shady respite from the sun and overlooks a native garden and the pool. While the dress is casual, the atmosphere (and menu) evokes island sophistication. Of course, you'll find plenty of fresh seafood, from ajillo shrimp and calamari to tuna tartare and the fresh catch of the day. 

But Tin Cup also offers an array of casual bites and American-Caribbean dishes with a Southern twist. Start your day noshing on a Key West Omelet, with shrimp and queso fresco tucked inside served with a mound of island potatoes. For a stay-in-your-bathing-suit lunch, try fish tacos and conch fritters or a fresh ahi mango salad by the pool. At dinner, go for the unexpected—the ancho-chili-rubbed Berkshire pork chop, haricot verts (a French variety of green beans), yucca, and freshly made pico de gallo. 

Top it all off with (what else?) a slice of creamy key lime pie for dessert.

Ready for a cold beverage? When you're in that Margaritaville state of mind, you know it's always 5 o'clock somewhere. At Tin Cup, you've got a choice of half a dozen margaritas, with catchy names like The Good Life and Licensed to Chill. But you'll also find Keys-inspired craft cocktails, like Iguana Mojito with raspberries, Oversees Highway blended with mango rum, and frozen concoctions like the popular Smathers Beach Daiquiri mixed with coconut water, fresh mango, and pineapple.

For a memorable twist on your tropical getaway, stay in the one-of-a-kind Jimmy Bucket suite.  This roomy one-bedroom king suite puts you poolside with a lovely, private balcony and two relaxing rocking chairs. The kicker? You get goodies delivered straight from the bar to your balcony, thanks to the custom pulley system that allows you to reel in the treats. So fun! Just text the resort when you're ready for the delivery and a kindly staff person will load up the wooden Jimmy Bucket with goodies (think freshly baked muffins and mimosa mixers) to enjoy al fresco. 

Starting at just an additional $150 per stay, the Jimmy Bucket Suite (which also features a Margarita Frozen Concoction Machine, limes, and a shaker of salt) also includes a keepsake Margaritaville cutting board, two branded shot glasses, and bucket of LandShark lagers. 

Opened in November 2021, the resort gives you easy access to the world-famous Smathers Beach, literally right across the street. Nestled along the southern shore of the island, this gorgeous stretch of sand offers plenty of amenities, including jet ski rentals, beach volleyball courts, chair and umbrella rentals, picnic areas, restrooms, shower facilities, and occasional food truck pitstops. As the day winds down, perch yourself on top of one of the boulders and watch the spectacular blaze of color as the sun melts into the turquoise waters.

Located just one mile from Key West International Airport and 10 minutes from Duval Street and the historic Downtown Seaport Harbor, the resort provides complimentary shuttle service to both—making your visit easy in, easy out. 
Lisa Beach is a seasoned freelance writer. Her work has been published in The New York Times, USA Today Go Escape, Parade, Good Housekeeping, Eating Well, and dozens more. Check out her writer's website at www.LisaBeachWrites.com.